To understand what's on Loudon Wainwright's mind, you need look no further than the titles of his albums: History, Therapy, I'm Alright, More Love Songs, Unrequited, Career Moves, Grown Man, Fame and Wealth, Last Man on Earth. Wry and witty, a skilled tunesmith with an arch sense of humor and a keen eye for the human condition, Wainwright's favorite subject is himself. Fortunately, there's a lot to explore.

"As long as you can stay self-absorbed enough, it works," he says (not entirely seriously) during a recent phone interview with The Indy. And although he seems unconcerned with the image issues facing a star of Mick Jagger's magnitude--he carries his own guitar to gigs like any typical folkie--his easygoing sense of humor doesn't fully reflect his internal struggle.

"I'm uncomfortable in my own skin," he admits, "but it's my own skin, and I know it. I just write about what I'm interested in. And I have been chronicling what has been going on in my life since I started writing songs in 1968."

In keeping with his experiences at the time, that first album had songs about going to boarding school and working in a macrobiotic restaurant. Since then, there've been songs about waitresses, lovers, anniversaries, being a dad, missing lovers, being an absent dad, Oedipal rivalries, doctors, hospitals, and--on Last Man on Earth--both losing his mother (in 1997) and coming to terms with becoming his father (who died in 1988).

"Maybe the fact that they're no longer with me frees me up to a certain extent," he says. "Some of the songs might be tough to sing if my parents were still alive, though I'd like to think they'd appreciate them."

Although Wainwright was born in Chapel Hill in 1946 (his father, Loudon Wainwright, Jr., was a UNC-Chapel Hill graduate and became a columnist and editor for Life magazine), he left North Carolina at age 3 before developing any cherished memories of the area. He grew up in Bedford, a rich Westchester County town outside of New York City, and currently resides in Brooklyn and Shelter Island, a tiny town off Long Island. But that hasn't stopped him from commenting on North Carolinians like Jesse Helms.

In Jesse Don't Like It, written when the senator was making a name for himself as a watchdog and critic of federally funded art, Wainwright observed, "The statue of David's all right with Jesse/'Cause Michelangelo gave him such a tiny pee-pee."

But he admits that Helms seems to have softened at bit since then.

"It's funny that he seems to be doing a series of recantings; he seems to be trying to be a nicer guy now that he's on the way out," Wainwright opines (this conversation, incidentally, took place prior to Helms' most recent hospitalization). "I wish him all the luck in the world in the afterlife," Wainwright adds with a laugh, "'cause he's going to need it."

The opus on Jesse was just one of the "topical songs" he's been commissioned to write by the likes of National Public Radio and ABC's Nightline. Two years ago, he released a collection of those tunes called Social Studies. But although songs about notable (or notorious) people--Tonya Harding, O.J. Simpson, Bill Clinton--tend to be as short-lived as their subjects, he remains unperturbed by the rising and consequent dimming of these "stars."

"That's the problem with topicality: It's topical," he says. "But it's fun to write about it at the time. There was a time when I would sing 'So Long, John Sununu,' and people would be really amused by it. Now they'd have to kind of remember the details." (Sununu was George Bush Sr.'s chief of staff.)

Last year he released The BBC Sessions, his best recordings from 30 years of live appearances on BBC radio. And Last Man on Earth, his first album of original material in four years, contains no "novelty songs," making it another kind of first for him. After all, this is the man whose first hit in 1972 was "Dead Skunk in the Middle of the Road" and who won Entertainment Weekly's 1996 Best Lyric award for a line from Grown Man's "I Wish I Was a Lesbian": "I wish I was a lesbian/I'd like to be a dyke/I would hang with k.d. lang/Mel Gibson, take a hike!"

Still, Wainwright remains willing to take on topics of a decidedly somber nature. He was living in New York City on Sept. 11.

"Because I live in Brooklyn Heights, I'm right across the East River from lower Manhattan, and there was this kind of gaping hole in the skyline," he recalls. "Initially, I thought I wasn't going to touch that subject because it's so huge, but I did find myself writing a song about it ["No Sure Way"], which I'll probably sing when I get down to Chapel Hill. It's about a subway ride into Chinatown that I took a week after Sept. 11. It's a description of what it felt like to go underneath the World Trade Center, and what was above me."

Whether about momentous events or personal tribulations, Wainwright's songs have one thing in common: They seem to arrive of their own accord.

"They're mysterious enough to me that I think that they just emerge somehow," he reckons. "There's craft involved, and you have to go digging for them sometimes, but the good ones seem to surface. I often use the analogy of fishing: You gotta be in the boat, and you gotta be able to get it into the boat, and to wait around for it. But it's mysterious why the damn thing takes the bait anyway."

Yet Wainwright doesn't feel like his fishing expeditions have been constrained by the narrowing of critical speech in the aftermath of last fall's tragedies. In the title track of Last Man on Earth,he announces, "I don't care which idiot runs this country."

"I remember singing that right after Sept. 11, when the new patriotism was really happening and thinking, 'Gee, I'd better ... ,'" he says. "So I had a little comic disclaimer before I sang the song, making fun of the fact that I am behind the man, so to speak. But I didn't not sing the song; I didn't not include the lyric. I think it's important to push buttons to test the audience. Making people uncomfortable, or making them think or even angering them, can be an interesting, valuable thing. It has to be done with care and craft, but I think it's part of being in that great tradition of balladeers and songwriters."

But being a part of that "great tradition" was not Wainwright's first choice: An actor is what he originally wanted to be, having studied theater at Carnegie Mellon University alongside contemporaries like Michael McKean and Albert Brooks. And while he's made his name as a singer-songwriter, he never goes for very long without performing in front of the cameras.

In 1975, Wainwright appeared in three episodes of M*A*S*H as singing surgeon Calvin Spaulding. He was David Letterman's original musical sidekick during the comedian's short-lived morning show that predated his late-night hit. He appears in the Sandra Bullock rehab film, 28 Days (performing two of the four songs he wrote for the soundtrack), and is also seen in Jackknife and The Slugger's Wife. Recently, he's done television appearances on Ally McBeal, as well as a regular turn as "Hal Karp" on Fox's Undeclared.

A consummate performer, Wainwright acknowledges enjoying his film and TV gigs. But did his keen sense of observation and willingness to deal with pain, self-evaluation and grief make the shallowness of Hollywood a bit too much to take?

"I'm so honest that the dishonesty is refreshing!" he announces, oozing sarcasm. "I'm wallowing in it; I love it. The surface, phony aspect to the town just suits me to a T."